- Iodine Acetate as a Mild Selective Agent for the Wagner–Meerwein Rearrangement in 3a,6-Epoxyisoindoles
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[Figure not available: see fulltext.] The iodine-initiated cationic skeletal Wagner–Meerwein rearrangement in tetrahydro-3a,6-epoxyisoindol-1-ones has been studied. It was shown that by the action of iodine acetate in acetic anhydride the reaction proceed
- Zaytsev, Vladimir P.,Mertsalov, Dmitriy F.,Trunova, Anastasiya M.,Khanova, Anastasiya V.,Nikitina, Eugeniya V.,Sinelshchikova, Anna А.,Grigoriev, Mikhail S.
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- Selective C-H Iodination of (Hetero)arenes
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Iodoarenes are versatile intermediates and common synthetic targets in organic synthesis. Here, we present a strategy for selective C-H iodination of (hetero)arenes with a broad functional group tolerance. We demonstrate the utility and differentiation to other iodination methods of supposed sulfonyl hypoiodites for a set of carboarenes and heteroarenes.
- Tanwar, Lalita,B?rgel, Jonas,Lehmann, Johannes,Ritter, Tobias
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supporting information
p. 5024 - 5027
(2021/06/30)
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- Identification of key functionalization species in the Cp?Ir(iii)-catalyzed-: ortho halogenation of benzamides
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Cp?Ir(iii) complexes have been shown to be effective for the halogenation of N,N-diisopropylbenzamides with N-halosuccinimide as a suitable halogen source. The optimized conditions for the iodination reaction consist of 0.5 mol% [Cp?IrCl2]2 in 1,2-dichlor
- Brown, Caleb A.,Guzmán Santiago, Alexis J.,Ison, Elon A.,Sommer, Roger D.
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supporting information
p. 16166 - 16174
(2020/12/03)
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- Iodine Monoacetate for Efficient Oxyiodinations of Alkenes and Alkynes
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A novel and inexpensive, environmentally friendly method for the preparation of iodine monoacetate is presented using iodine and Oxone in acetic acid/acetic anhydride. The reagent is used in a highly efficient approach for the regio- and diastereoselective iodo-acetoxylation of alkenes and alkynes in a simple one-pot process.
- Hokamp, Tobias,Storm, Alena Therese,Yusubov, Mekhman,Wirth, Thomas
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supporting information
p. 415 - 418
(2017/10/30)
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- Visible-Light-Mediated Remote γ-C(sp3)-H Functionalization of Alkylimidates: Synthesis of 4-Iodo-3,4-dihydropyrrole Derivatives
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An efficient and environmentally friendly synthetic approach toward functionalized dihydropyrrole derivatives is reported. The developed protocol proceeds via chemoselective intramolecular N-C bond formation of alkylimidates through 1,5-hydrogen atom transfer from in situ generated imidate N-radicals. The major advantage of this designed strategy lies in the choice of starting materials, mild reaction conditions, high chemo- and diastereoselectivity, clean source of energy, and good functional group tolerance. Further, 4-iododihydropyrroles could be easily transformed into a variety of useful derivatives.
- Kumar, Yogesh,Jaiswal, Yogesh,Kumar, Amit
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supporting information
p. 4964 - 4969
(2018/08/24)
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- PIDA-I2 mediated direct vicinal difunctionalization of olefins: Iodoazidation, iodoetherification and iodoacyloxylation
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Iodinium cation (I+ or IOAc) was produced from the combination of phenyliodine diacetate (PIDA) and iodine. I+ facilitated the direct vicinal difunctionalization of olefins to α-azido, α-trideuteriomethoxy, α-2,2,2-trifluoroethoxy and α-acyloxy alkyl iodides via cation-π interaction at room temperature and under transition-metal free conditions.
- Achar, Tapas Kumar,Maiti, Saikat,Mal, Prasenjit
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p. 4654 - 4663
(2016/06/09)
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- Cleavage Reactions of some Phenyltin Compounds with Iodine Halides, -Pseudohalides and -Carboxylates
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Cleavage reactions of iodinehalides, -pseudohalides IX (X = Cl, Br, NCO, NCS, N3 and CN) with Ph3SnCp yield triphenyltinhalides, -pseudohalides (Ph3SnX) indicating cleavage of Cp-Sn bond in preference to Ph-Sn bond, and cleavage reactions of iodine carboxylates IX′ (X′ = CH3OCO, C5H5OCO, C6H5CH2OCO, o-NH2C6H4OCO, o-CIC6H4OCO, p-NO2C6H4OCO, p-NH2C6H4OCO, C6H5CH =CHOCO) (in situ) with Ph3SnCl give hitherto unknown diphenylchlorotin carboxylates (Ph2SnX′Cl) indicating cleavage of Ph-Sn bond in preference to Cl-Sn bond. On the basis of the results, it is predicated that these diphenylchlorotin carboxylates possess bridging carboxylate groups (inter-molecularly chelated structure) in the solid state, whereas in solution they contain chelated carboxylate groups (intra-molecularly chelated structures).
- Srivastava,Singh,Tangri,Sinha,Bajpai
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p. 443 - 445
(2007/10/03)
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